Potassium Iodide → HCID 23036358, compound

HRID 1709916Notes

Reaction equation

HRID 1709916 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[C:22]([C:25]1[CH:35]=[CH:34][C:28]([O:29][CH2:30][CH2:31][CH2:32]Cl)=[C:27]([O:36][CH3:37])[CH:26]=1)(=[O:24])[CH3:23].C(=O)(O)[O-].[Na+].[I-].[K+].[C:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]/[C:48]([OH:50])=[O:49]>C(O)CCC.CO.CCOCC>[C:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]/[C:48]([OH:50])=[O:49].[F:1][C:2]1[CH:3]=[C:4]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH:9]2[CH2:10][CH2:11][N:12]([CH2:32][CH2:31][CH2:30][O:29][C:28]3[CH:34]=[CH:35][C:25]([C:22](=[O:24])[CH3:23])=[CH:26][C:27]=3[O:36][CH3:37])[CH2:13][CH2:14]2)[CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 444972Fumaric AcidHCID 516892Sodium BicarbonateHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 15093838HCID 15093838, compound

Product 1

HCID 23036358HCID 23036358, compoundYield 15.1%

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5.32 g (0.019 mole) of 4-[bis(3-fluorophenyl)methyl]piperidine, 4.80 g (0.020 mole) of 3-(4-acetyl-2-methoxyphenoxy)-1-chloropropane, 2.4 g (0.029 mole) of sodium bicarbonate and 0.20 g (0.0012) mole of potassium iodide in 400 ml of 1-butanol was heated at reflux for 23 hr. The solvent was removed in vacuo and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was dried over magnesium sulfate and the solvent was removed in vacuo to give an oil. This was dissolved in methanol and the solution was treated with an excess of fumaric acid. Ether was added and a gum formed. The gum was triturated with acetonitrile to give 1.75 g (15.1%) of the title compound as a white crystalline solid, mp 180°-181° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 23 hr
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between methylene chloride and dilute sodium hydroxide
  5. dry with materialThe methylene chloride solution was dried over magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customto give an oil
  8. customa gum formed
  9. customThe gum was triturated with acetonitrile

Sources & evidence

ORD record
ord-42135b1d2c01456aa88da38a7bf43c3d
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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